Methyl iodide → 5-(N-methyl-N-methylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine

HRID 1072209Notes

Reaction equation

HRID 1072209 reaction equation
[CH3:1][S:2]([NH:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)(=[O:4])=[O:3].[H-].[Na+].I[CH3:20]>C1COCC1>[CH3:20][N:5]([CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)[S:2]([CH3:1])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 223917905-Methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine

Product 1

HCID 223917805-(N-methyl-N-methylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepineYield 31.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.54 g (13.4 mmol) of methanesulfonyl chloride were added dropwise with ice cooling to a solution of 2.0 g (12.2 mmol) of 5-amino-2,3,4,5-tetrahydro-1-benzoxepine (Example 6b) and 3.7 g (36.6 mmol triethylamine in 40 ml of THF. The mixture was allowed to come to RT and was stirred overnight and treated with 50 ml of water, and the THF was distilled off in vacuo. The residue was diluted with a further 50 ml of water and stirred for 3 h, and the deposited product was filtered off with suction. After drying in vacuo, 2.2 g of 5-methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine were obtained, m.p. 105-106° C. b) A solution of 1.1 g (6.2 mmol) of 5-methylsulfonylamino-2,3,4,5-tetrahydro-1-benzoxepine in 15 ml of THF was added dropwise to a suspension of 0.23 g (6.2 mmol) of 80 percent sodium hydride in 10 ml of THF. After 2 h at RT, 0.94 g (6.7 mmol) of iodomethane were added and the mixture was stirred overnight at RT. After distilling off the solvent in vacuo, the residue was taken up in EA, and the solution was washed with dilute hydrochloric acid and water, dried over magnesium sulfate and concentrated. Subsequent recrystallization of the product from isopropanol yielded 0.5 g of 5-(N-methyl-N-methylsulfonylamino)-2,3,4,5-tetrahydro-1-benzoxepine, m.p. 143-145° C.

Workup

  1. distillationAfter distilling off the solvent in vacuo
  2. washthe solution was washed with dilute hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customSubsequent recrystallization of the product from isopropanol

Sources & evidence

ORD record
ord-e06b05c337e94f199ea291323bddc1d4
Source dataset
uspto-grants-2005_06
Patent number
US06908947B2

Reaction notes

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